{"id":9841,"date":"2013-03-17T08:59:32","date_gmt":"2013-03-17T08:59:32","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=9841"},"modified":"2019-11-17T08:42:11","modified_gmt":"2019-11-17T08:42:11","slug":"the-mysterious-aromatic-structure-of-n-butyl-lithium","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9841","title":{"rendered":"The mysterious (aromatic) structure of n-Butyl lithium."},"content":{"rendered":"
\n

n-Butyl lithium<\/a> is hexameric<\/a> in the solid state[1]<\/a><\/span> and in cyclohexane solutions. Why? Here I try to find out some of its secrets.<\/p>\n

\"SUHBEC.

SUHBEC. CLICK FOR 3D.<\/p><\/div>\n

The crystal structure reveals the following points of interest:<\/p>\n

    \n
  1. Six lithium atoms form a cluster with triangular faces.<\/li>\n
  2. An off-centre carbanion caps a triangular lithium face.<\/li>\n
  3. Four of the butyl groups are in a fully extended antiperiplanar conformation<\/li>\n
  4. But two di-axial n-butyl exhibit a gauche conformation.<\/li>\n<\/ol>\n

    The lithium cluster has twelve electrons available for bonding; if the Li is considered as Li+<\/sup>, balanced by six C–<\/sup> carbanions, the twelve electrons come from the six carbon lone pairs pointing towards each of six triangular faces. An ELF analysis<\/a> can help identify how these twelve electrons are arranged. Shown below is the environment of a single Li-face, with the ELF basin ringed. It integrates to 2.08 electrons. So each tetrahedral cluster of three lithiums and one carbanion could be considered as a\u00a0two-electron-four-centre<\/em>\u00a0bond, perhaps a natural progression from the\u00a0two-electron-three-centre<\/em>\u00a0bonding found in a slightly less electron deficient system such as diborane.\u00a0<\/p>\n

    \"ELF

    ELF basins. Click for 3D<\/p><\/div>\n

    NBOs (natural bond orbitals) reflect this character. An NBO represents a localised two-electron orbital, and analysis<\/a> indeed reveals six such orbitals, each having the form shown below.<\/p>\n

    \"NBO.

    NBO. Click for 3D.<\/p><\/div>\n

    This picture in turn leads us to identify this system as spherically aromatic[2]<\/a><\/span>. The three-dimensional equivalent of the H\u00fcckel rule is that any system with 2(N+1)2<\/sup> \u03c3 or \u03c0 electrons (or both) in a cluster can be considered aromatic\/diatropic. In this case, N=0 and hence the magic count is 2 for each of the six CLi3<\/sub> tetrahedra. The diatropic ring current might be manifested in the computed<\/a> 1<\/sup>H NMR chemical shifts of the CH2<\/sub>–<\/sup> protons (-0.8ppm). Aromaticity does not immediately spring to mind with the name n-butyl lithium,\u00a0but this unprepossessing molecule has six aromatic regions!<\/p>\n

    Each lithium atom is in turn hemispherically surrounded by three of these 2.08 electron basins (below, although the ELF centroid is very much biased towards the carbon, indicating considerable ionicity). What wonderful electronic economy! Despite there being only twelve electrons to be shared amongst six lithium atoms, each lithium manages nevertheless to surround itself with 6.24 electrons. All crammed into one half sphere, leaving a nice coordination hole; n-butyl lithium is after all a highly reactive species (even as a hexamer).<\/p>\n

    \"n-butyl-ELF1\"<\/p>\n

    I want to finish by exploring the observation that two of the six n-butyl groups adopt a gauche conformation. In free n-butane itself, around 31% of the population adopts this shape, which curiously is around the same proportion as is found in the hexameric structure of n-butyl lithium. More generally, a search of the Cambridge database for compounds containing such groups reveals the following distribution; about 1 in 7.<\/p>\n

    \"Gauche\"<\/p>\n

    Well, when you deprive a molecule of electrons, as any species with lithium must invariably suffer from, it is wonderful how the system responds. In this sense, a hexameric structure seems a very natural outcome. And it has brought us the two-electron-four-centre<\/em> bond and the associated spherical\u00a0aromaticity<\/em>, both of which are a nice bonus.<\/p>\n

    References<\/h2>\n
    1. T. Kottke, and D. Stalke, \"Structures of Classical Reagents in Chemical Synthesis: (<i>n<\/i>BuLi)<sub>6<\/sub>, (<i>t<\/i>BuLi)<sub>4<\/sub>, and the Metastable (<i>t<\/i>BuLi \u00b7 Et<sub>2<\/sub>O)<sub>2<\/sub>\", Angewandte Chemie International Edition in English<\/i>, vol. 32, pp. 580-582, 1993. https:\/\/doi.org\/10.1002\/anie.199305801<\/a>\n\n<\/li>\n
    2. A. Hirsch, Z. Chen, and H. Jiao, \"Spherical Aromaticity inIh Symmetrical Fullerenes: The 2(N+1)2 Rule\", Angewandte Chemie<\/i>, vol. 39, pp. 3915-3917, 2000. https:\/\/doi.org\/10.1002\/1521-3773(20001103)39:21<3915::aid-anie3915>3.0.co;2-o<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

      n-Butyl lithium is hexameric in the solid state and in cyclohexane solutions. Why? Here I try to find out some of its secrets. The crystal structure reveals the following points of interest: Six lithium atoms form a cluster with triangular faces. An off-centre carbanion caps a triangular lithium face. Four of the butyl groups are […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":true,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"activitypub_content_warning":"","activitypub_content_visibility":"","activitypub_max_image_attachments":5,"activitypub_interaction_policy_quote":"anyone","activitypub_status":"","footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2},"jetpack_post_was_ever_published":false},"categories":[4],"tags":[144,49,17,1028,1009,1008,373],"ppma_author":[2661],"class_list":["post-9841","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-cambridge","tag-chemical-shifts","tag-conformational-analysis","tag-cyclohexane-solutions","tag-hexameric","tag-spherical-aromaticity","tag-tutorial-material"],"yoast_head":"\nThe mysterious (aromatic) structure of n-Butyl lithium. - Henry Rzepa's Blog<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9841\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The mysterious (aromatic) structure of n-Butyl lithium. - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"n-Butyl lithium is hexameric in the solid state and in cyclohexane solutions. Why? Here I try to find out some of its secrets. The crystal structure reveals the following points of interest: Six lithium atoms form a cluster with triangular faces. An off-centre carbanion caps a triangular lithium face. Four of the butyl groups are […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9841\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa's Blog\" \/>\n<meta property=\"article:published_time\" content=\"2013-03-17T08:59:32+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2019-11-17T08:42:11+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/03\/SUHBEC.jpg\" \/>\n<meta name=\"author\" content=\"Henry Rzepa\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Henry Rzepa\" \/>\n\t<meta name=\"twitter:label2\" content=\"Estimated reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"3 minutes\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"The mysterious (aromatic) structure of n-Butyl lithium. - Henry Rzepa's Blog","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9841","og_locale":"en_GB","og_type":"article","og_title":"The mysterious (aromatic) structure of n-Butyl lithium. - Henry Rzepa's Blog","og_description":"n-Butyl lithium is hexameric in the solid state and in cyclohexane solutions. Why? Here I try to find out some of its secrets. The crystal structure reveals the following points of interest: Six lithium atoms form a cluster with triangular faces. An off-centre carbanion caps a triangular lithium face. 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Investigating the mechanism using quantum calculations poses some interesting challenges, ones I have not previously discussed on this blog. My model will\u2026","rel":"","context":"In "Hypervalency"","block_context":{"text":"Hypervalency","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=7"},"img":{"alt_text":"SUHBEC. CLICK FOR 3D.","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/03\/SUHBEC.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":29725,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29725","url_meta":{"origin":9841,"position":1},"title":"The mechanism of borohydride reductions. Part 2: 4-t-butyl-cyclohexanone – Dispersion induced stereochemistry.","author":"Henry Rzepa","date":"October 21, 2025","format":false,"excerpt":"Part one of this topic was posted more than ten years ago. I clearly forgot about it, so belatedly, here is part 2 - dealing with the stereochemistry of the reduction of tert-butyl-cyclohexanone by borohydride in water. The known stereochemistry is nicely summarised in this article, along with an extensive\u2026","rel":"","context":"In "reaction mechanism"","block_context":{"text":"reaction mechanism","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1086"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":8588,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=8588","url_meta":{"origin":9841,"position":2},"title":"Why is the Sharpless epoxidation enantioselective? Part 1: a simple model.","author":"Henry Rzepa","date":"December 9, 2012","format":false,"excerpt":"Sharpless epoxidation converts a prochiral allylic alcohol into the corresponding chiral epoxide with > 90% enantiomeric excess,. Here is the first step in trying to explain how this magic is achieved. The scheme above shows how (achiral) prop-2-enol is converted using the asymmetric catalyst\u00a0(R,R)-diethyl tartrate \u00a0and t-butyl hydroperoxide as oxidant\u2026","rel":"","context":"In "Interesting chemistry"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2012\/12\/sharpless.gif?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":15048,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=15048","url_meta":{"origin":9841,"position":3},"title":"I’ve started so I’ll finish. The mechanism of diazo coupling to indoles – forty (three) years on!","author":"Henry Rzepa","date":"December 24, 2015","format":false,"excerpt":"The BBC TV quiz series Mastermind\u00a0was first broadcast in the UK in 1972,\u00a0the same time\u00a0I was starting to investigate\u00a0the mechanism of diazocoupling to substituted indoles as part of my Ph.D. researches. The BBC program became known\u00a0for the\u00a0catch phrase\u00a0I've started so I'll finish;\u00a0here I will try to follow this precept with\u2026","rel":"","context":"In "Historical"","block_context":{"text":"Historical","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=565"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":19499,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=19499","url_meta":{"origin":9841,"position":4},"title":"Never mind main group “hypervalency”, what about transition metal “hypervalency”?","author":"Henry Rzepa","date":"March 18, 2018","format":false,"excerpt":"I have posted often on the chemical phenomenon known as hypervalency, being careful to state that as defined it applies just to \"octet excess\" in main group elements. But what about the next valence shell, occurring in transition metals and known as the \"18-electron rule\"? You rarely hear the term\u2026","rel":"","context":"In "Hypervalency"","block_context":{"text":"Hypervalency","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=7"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2018\/03\/NiPP-987x1024.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":29410,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29410","url_meta":{"origin":9841,"position":5},"title":"Energy decomposition analysis of hindered alkenes: Tetra t-butylethene and others.","author":"Henry Rzepa","date":"August 13, 2025","format":false,"excerpt":"In the previous post, I introduced the N=N double bond in nitrosobenzene dimer, arguing that even though it was a formal double bond, its bond dissociation energy made it nonetheless a very weak double bond! This was backed up by a technique known as energy decomposition analysis or EDA. Here\u2026","rel":"","context":"In "Interesting chemistry"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]}],"jetpack_likes_enabled":false,"authors":[{"term_id":2661,"user_id":1,"is_guest":0,"slug":"admin","display_name":"Henry Rzepa","avatar_url":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g","0":null,"1":"","2":"","3":"","4":"","5":"","6":"","7":"","8":""}],"_links":{"self":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/9841","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=9841"}],"version-history":[{"count":44,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/9841\/revisions"}],"predecessor-version":[{"id":21471,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/9841\/revisions\/21471"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=9841"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=9841"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=9841"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=9841"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}